The present invention relates to pyrone compounds and their pesticidal use.
JP51-19126A discloses that some pyrone compounds have insecticidal/acaricidal activity. However, their compounds are not satisfactorily effective for controlling harmful pests.
The present invention provides a compound given by formula 
wherein R represents a trifluoromethyl group, hydrogen atom or methyl group, a pesticidal composition comprising it as an active ingredient and a method for controlling pests comprising applying it to pests or a place where pests inhabit.
The present compound has an excellent pesticidal activity.
A process for producing the present compound is explained below.
The present compound can be produced by the method given by the scheme below, namely reaction of 4-hydroxy-6-methyl-2-pyrone given by formula (2) with a carboxylic acid given by formula (3): 
wherein R has the same meaning above.
The reaction is usually carried out in a solvent in the presence of a condensing agent (e.g. dicyclohexylcarbodiimide) and 4-dimethylaminopyridine.
Examples of the solvent to be used for the reaction include aliphatic hydrocarbons such as hexane, heptane, octane and nonane; aromatic hydrocarbons such as toluene, xylene and mesitylene; halogenated hydrocarbons such as chlorobenzene, dichlorobenzene and benzotrifluoride; ethers such as diisopropyl ether, 1,4-dioxane, tetrahydrofuran, ethylene glycol dimethyl ether and diethylene glycol dimethyl ether; acid amides such as N,N-dimethylformamide and N,N-dimethylacetamide; sulfur-containing solvents such as dimethyl sulfoxide and sulfolane; and mixtures thereof.
In the reaction, the amount ratio of the compound given by formula (3) is 0.7 to 1.5 moles based on 1 mole of the compound given by formula (2).
The amount ratio of the reagents is 1 to 5 moles of the condensing agent and 0.01 to 1 mole of 4-dimethylaminopyridine based on 1 mole of the compound given by formula (2).
The reaction temperature is usually within a range from 0xc2x0 C. to 100xc2x0 C., and the reaction time is usually within a range from 1 to 48 hours though it depends on the reaction temperature.
After the completion of the reaction, the reaction mixture can be, for example, subjected to a filtration, washing the filtrate with an acidic water, drying and then concentration, optionally purification such as chromatography, to give the present compound as an isolated product.
Examples of the pests against which the present compound exhibits a control effect include the following arthropods: Hemipteran pests: Delphacidae (planthoppers) [e.g. Laodelphax striatellus (small brown planthopper), Nilaparvata lugens (brown planthopper) and Sogatella furcifera (white-backed rice planthopper)], Deltocephalidae (leafhoppers) [e.g. Nephotettix cincticeps, Nephotettix virescens and Recilia dorsalis], Aphididae (aphids), stinkbugs, Aleyrodidae (whiteflies), scales, Tingidae (lace bugs) and Psyllidae (suckers);
Lepidopteran pests: Pyralidae [e.g. Chilo suppressalis (rice stem borer), Cnaphalocrocis medinalis (rice leafroller) and Plodia interpunctella (Indian meal moth)], Noctuidae [e.g. Spodoptera litura (tobacco cutworm), Pseudaletia separata (rice armyworm), Mamestra brassicae (cabbage armyworm), Plusiinae, Agrotis spp. containing Agrotis segetum (turnip cutworm) and Agrotis ipsilon (black cutworm), Helicoverpa spp. and Heliothis spp.], Pieridae [e.g. Pieris rapae], Tortricidae [e.g. Adoxophyes spp.], Carposinidae, Lyonetiidae, Lymantriidae, Yponameutidae [e.g. Plutella xylostella], Hesperiidae [e.g. Parnara guttata], Tineidae [e.g. Tinea translucens (casemaking clothes moth) and Tineola bisselliella (webbing clothes moth)];
Dipteran pests: Culex spp. [e.g. Culex pipiens pallens and Culex tritaeniorhynchus], Aedes spp. [e.g. Aedes aegypti (yellow fever mosquito) and Aedes albopictus], Anopheles spp. [e.g. Anopheles sinensis], Chironomidae (midges), Muscidae [e.g. Musca domestica (housefly), Muscina stabulans (false housefly) and Fannia canicularis (little house fly)], Calliphoridae, Sarcophagidae, Anthomyiidae [e.g. Delia platura (seedcorn maggot) and Delia antiqua (onion maggot)], Tephritidae (fruit flies), Drosophilidae (vinegar flies), Psychodidae (sand flies), Tabanidae, Simuliidae (black flies), Stomoxyidae (stable flies), Phoridae and Ceratopogonidae (biting midges);
Coleopteran pests: corn rootworms [e.g. Diabrotica virgifera virgifera (western corn rootworm) and Diabrotica undecimpunctata howardir (southern corn rootworm)], Scarabaeidae [e.g. Anomala cuprea and Anomala rufocuprea], Curculionidae (weevils) [e.g. Sitophilus zeamais (maize weevil) and Lissorhoptrus ozyzophilus (ricewater weevil), Dermestidae [e.g. Authrenus verbasci and Attagenus unicolor japonicus], Tenebrionidae (darkling beetles) [e.g. Tenebrio molitor (yellow mealworm) and Tribolium castaneum (red flour beetle)], Chrysomelidae (leaf beetles) [e.g. Oulema oryzae (rice leaf beetle), Phyllotreta striolata (striped flea beetle) and Aulacophora femoralis (cucurbit leaf beetle), Anobiidae, Coccinellidae (ladybirds). [e.g. Epilachna vigintioctopunctata], Lyctidae (powderpost beetles), Bostrychidae, Cerambycidae and Staphylinidae [e.g. Paederus fuscipes]; 
Dictyopteran pests: Blattella gezmanica (German cockroach), Periplaneta fuliginosa (smokybrown cockroach), Periplaneta americana (American cockroach), Periplaneta brunnea (brown cockroach) and Blatta orientalis and so on;
Thysanopteran pests: Thripidae [e.g. Thrips palmi, Frankliniella occidentalis (western flower thrips) and Thrips hawaiiensis (flower thrips)];
Hymenopteranpests: Formicidae (ants), Vespidae [e.g. hornets and long-legged wasps], Bethylidae and Tenthredinidae (sawflies) [e.g. Athalia japonica (cabbage sawfly)];
Orthopteran pests: Gryllotalpidae (mole crickets) and Acrididae (grasshoppers);
Siphonapteran pests: Ctenocephalides canis (dog flea), Ctenocephalides felis (cat flea) and Pulex irritans (human flea);
Anopluran pests: humanus corporis, Pediculus capitis and Phthirus pubis (crab louse);
Isopteran pests; Reticulitezmes speratus and Coptotezmes fozmosanus; 
Acarina pests: Tetranychidae (spider mites) [e.g. Tetranychus cinnabarinus (carmine spider mite), Tetranychus urticae (two-spotted spider mite), Tetranychus kanzawai (Kanzawa spider mite), Panonychus citri (citrus red mite) and Panonychus ulmi (European red mite)], Ixodidae [e.g. Boophilus microplus and Haemaphysalis longiconis], Acaridae [e.g. Tyrophagus putrescentiae (copra mite) and Aleuroglyphus ovatus], Dermanyssidae [e.g. Dermatophagoides farinae (American house dust mite) and Dermatophagoides ptrenyssnus], Glycyphagidae [e.g. Glycyphagus privates, Glycyphagus domesticus and Glycyphagus destructor], Cheyletidae [e.g. Cheyletus malaccensi and Cheyletus fortis], Tarsonemidae, Chortoglyphus spp. and Haplochthonius spp.;
Isopoda pests: wood louse [e.g. Porcellio scaber and Porcellionides pruinosus] and pill-bugs [e.g. Armadillidium vulgare]. 
The pesticidal composition of the present invention comprises the present compound and an inert carrier, such as solid carrier, liquid carrier, gaseous carrier and/or bait material (poison bait material). The present compound may be impregnated with a base material (e.g. porous ceramic board, non-woven cloth, paper, mosquito-coil base). Further, the pesticidal composition of the present invention optionally comprises a surfactant or the other auxiliary to be formulated to oil solutions, emulsifiable concentrates, wettable powders, flowable formulations, granules, dusts, aerosols, foggings, heating fumigants, smokings, poison baits, microcapsule formulations, ULV formulations, spot-on formulations, pour-on formulations, shampoo formulations, sheet formulations, resin formulations and so on.
These formulations usually include the present compound as an active ingredient in an amount of 0.01 to 95% by weight.
Examples of the solid carrier to be used for the formulation include fine powder or granules of clays (e.g. kaolin clay, diatomaceous earth, synthetic hydrated silicon oxide, bentonite, Fubasami clay, acid clay), talc, ceramics, fertilizer (e.g. ammonium sulfate, ammonium phosphate, ammonium nitrate, ammonium chloride, urea) and other inorganic minerals (e.g. sericite, quartz, sulfur, activated carbon, calcium carbonate, hydrated silicon oxide).
Examples of the liquid carrier include water, alcohols (e.g. methanol, ethanol), ketones (e.g. acetone, methyl ethyl ketone), aromatic hydrocarbons (e.g. toluene, xylene, ethylbenzene, methylnaphthalene), aliphatic hydrocarbons (e.g. hexane, cyclohexane, kerosene, gas oil), esters (ethyl acetate, butyl acetate), nitriles (e.g. acetonitrile, isobutyronitrile), ethers (e.g. diisopropyl ether, dioxane), acid amides (e.g. N,N-dimethylformamide, N,N-dimethylacetamide), halogenated hydrocarbons (dichloromethane, trichloroethane, carbon tetrachloride), organic sulfur compounds (e.g. dimethyl sulfoxide) and vegetable oils (e.g. soybean oil, cottonseed oil).
Examples of the gaseous carrier include fluorocarbons, butanegas, LPG (liquefied petroleum gas), dimethyl ether and carbon dioxide.
Examples of the surfactant include alkyl sulfates, alkylsulfonates, alkylarylsulfonates, alkyl aryl ethers, polyoxyethylenealkyl aryl ethers, polyethylene glycol ethers, polyhydric alcohol esters and sugar alcohol derivatives.
Examples of the other auxiliaries include sticking agents, dispersing agent and stabilizing agents, typically, casein, gelatin, polysaccharides (e.g. starch, gum arabic, cellulose derivatives, alginic acid), lignin derivatives, synthetic water-soluble polymers (e.g. polyvinyl alcohol, polyvinylpyrrolidone, polyacrylic acids), PAP (acid isopropyl phosphate), BHT (2,6-di-tert-butyl-4-methyphenol), BHA (mixture of 2-tert-butyl-4-methoxyphenol and 3-tert-butyl-4-methoxyphenol), vegetable oils, mineral oils, fatty acids and esters of fatty acid.
The base material of the poison baits includes a bait component (e.g. grain powder, vegetable oil, sugar, cellulose), an antioxidant (e.g. dibutylhydroxytoluene, nordihydroguaiaretic acid), a preservative (e.g. dehydroacetic acid), a substance for preventing erroneous eating from children and pets (e.g. red pepper powder), a pest-attractant flavor (e.g. cheese flavor, onion flavor, peanut oil).
When the present pesticidal composition is applied for controlling agricultural or forestry pests, the application dosage of the present compound is usually 1 to 10 000 g per 1 hectare. Emulsifiable concentrates, wettable powders and flowable formulations are diluted with water to the concentration of 10 to 10000 ppm and applied. Granules and dusts are usually used as prepared. These formulations can be applied directly to the pests or to plants which are crops to be protected from the pests. Further, they may be applied to soil for controlling the pests living in the soil.
When the present pesticidal composition is applied for hygienic use, emulsifiable concentrates, wettable powders and flowable formulations are diluted with water to the concentration of 0.01 to 10000 ppm and applied to pests or a place the pests inhabit. Oil solutions, aerosols, smokings and poison baits are applied to pests or a place the pests inhabit as prepared. Fumigants are applied by heating to volatile the active ingredient at a place the pests inhabit. The application dosage of the present compound is usually 0.001 to 5 g/m2 of the floor or 0.01 to 10 g/m3 of the space.
The present pesticidal composition can be used together with the other insecticide, acaricide, nematocide, fungicide, herbicide, plant growth regulator, synergist, fertilizer, soil-improving agent, animal food and so on.
Examples of the insecticides, acaricides and nematocides include organophosphorus compounds such as fenitrothion, fenthion, diazinon, chlorpyrifos, acephate, methidathion, disulfoton, DDVP, sulprofos, cyanophos, dioxabenzofos, dimethoate, phenthoate, malathion, trichlorfon, azinphos-methyl, monocrotophos and ethion; carbamate compounds such as BPMC, benfracarb, propoxur, carbosulfan, carbaryl, methomyl, ethiofencarb, aldicarb, oxamyl and fenothiocarb; pyrethroid compounds such as etofenprox, fenvalerate, esfenvalerate, fenpropathrin, cypermethrin, permethrin, cyhalothrin, deltamethrin, cycloprothrin, fluvalinate, bifenthrin, tralomethrin, silafluofen, d-phenothrin, d-allethrin, cyphenothrin, d-resmethrin, acrinathrin, cyfluthrin, tefluthrin, transfluthrin, tetramethrin, allethrin, prallethrin, empenthrin, imiprothrin and d-furamethrin; thiadiazine derivatives such as buprofezin; nitroimidazolidine derivatives; nereistoxin derivatives such as cartap, thiocyclam and bensultap; neonicotinoid compounds such as acetamiprid, thiamethoxam and thiacloprid; chlorinated hydrocarbons such as endosulfan, xcex3-BHC and DDT; benzoylphenylurea compounds such as chlorfluazuron, teflubenzuron and flufenoxuron; formamidine derivatives such as amitraz and chlordimeform; thiourea derivatives such as diafenthiuron; phenylpyrazole compounds; metoxadiazone; bromopropylate; tetradifon; chinomethionat; propargite; fenbutatin oxide; hexythiazox; clofentezine; pyridaben; fenpyroximate; tebufenpyrad; polynactins complex [tetranactin, dinactin and trinactin]; pyrimidifen; milbemectin; abamectin; ivermectin and azadirachtin [AZAD].